Patent GB-600851-A (GB)
Title: Production of substituted propyldiamines and particularly their acridine compounds
Filed: 1945-08-03
Abstract: 2 - Methoxy - 6 - chloro - 9 - [21 - substituted-31-(disubstituted-amino)propylamino] acridines of the general formula <FORM:0600851/IV(b)/1> wherein R and R1 represent different, non-tertiary, saturated hydrocarbon radicals and the sum of their carbon atoms does not exceed 10, and R11 represents hydrogen or the methyl radical, are prepared by condensing 2-methoxy-6 : 9-dichloroacridine with a diamine of the general formula <FORM:0600851/IV(b)/2> where R, R1 and R11 have the significance indicated above.  The bases may be converted to their salts by the addition of acids.  In examples (1) to (5), 2-methoxy-6 : 9-dichloroacridine is condensed with 21-hydroxy-21-methyl - 31 - (methyl - n - propylamino) -, 21-hydroxy - 31 - (n - propyl - iso - propylamino)-, 21 - hydroxy - 31 - (n - butylethylamino)-, 21-hydroxy - 31 - (methyl - n - propylamino)-, and 21 - hydroxy - 21 - methyl - 31 - (ethylcyclopentylamino) - propylamines and the substituted acridines are converted into their dihydrohalides; (8) the substituted acridines prepared as in (1) to (5) are converted into their dihydrobromides, sulphates, nitrates, phosphates, lactates or propionates.  Diamines of the general formula <FORM:0600851/IV(b)/3> where R, R1 and R11 have the above significance, are prepared (i) when R11 is hydrogen by reacting a secondary amine with 1-chloro-2 : 3-epoxypropane in a solvent, e.g. methoxyethanol and adding potassium phthalimide and sodium iodide and hydrolysing the resulting substituted propylphthalimide and (ii) when R11 represents the methyl radical, 1-chloro-2-methyl-2 : 3-epoxypropane is reacted as in (1). In examples (1) to (5), the preparation of the following diamines is described: 2 - hydroxy - 2 - methyl - 3 - (methyl - n - propylamino) -, 2-hydroxy - 3 - (n - propyl - iso - propylamino) -, 2 - hydroxy - 3 - (n - butylethylamino)-, 2-hydroxy - 3 - (methyl - n - propylamino)-, and 2 - hydroxy - 2 - methyl - 3 - (ethylcyclopentylamino)-propylamines.  Ethylcyclopentylamine is prepared by reducing a mixture of ethylamine and cyclopentanone with hydrogen in the presence of Raney nickel catalyst and under heat and pressure.ALSO: 2-Methoxy-6-chloro-9-[21-substituted-31-(disubstituted -amino) propylamino]-acridines of the general formula <FORM:0600851/IV (c)/1> wherein R and R1 represent different, non-tertiary, saturated hydrocarbon radicals and the sum of their carbon atoms does not exceed 10, and R11 represents hydrogen or the methyl radical, are prepared by condensing 2-methoxy-6 : 9-dichloroacridine with a diamine of the general formula <FORM:0600851/IV (c)/2> where R, R1 and N11 have the significance indicated above.  The bases may be converted to their salts by the addition of acids.  In examples (1) to (5), 2-methoxy-6 : 9-dichloroacridine is condensed with 21-hydroxy-21-methyl - 31 - (methyl - n - propylamino)-, 21-hydroxy-31-(n-propyl-iso-propylamino)-, 21-hydroxy-31-(n-butylethylamino)-, 21-hydroxy-31-(methyl-n-propylamino)-, and 21-hydroxy-21-methyl-31-(ethylcyclopentylamino) -propylamines and the substituted acridines are converted into their dihydrohalides; (8) the substituted acridines prepared as in (1) to (5) are converted into their dihydrobromides, sulphates, nitrates, phosphates, lactates or propionates.